Methylamine → HCID 66744496, compound

HRID 1959466Notes

Reaction equation

HRID 1959466 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:25][CH:26]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=2)=[N:11][N:12]=1.[CH3:31][NH2:32]>C1COCC1.CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:25][CH:26]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:32][CH3:31])=[CH:15][CH:14]=2)=[N:11][N:12]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 66745328HCID 66745328, compound

Product 1

HCID 66744496HCID 66744496, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[4-[5-amino-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,6-dihydro-2H-pyridin-1-yl]propan-1-one (20 mg, 0.04 mmol) and a solution of methanamine (107 μL of 2 M, 0.21 mmol) in THF was heated at 65° C. for 6 h. The reaction mixture was allowed to cool to room temperature and the solvents were evaporated under reduced pressure. The crude material obtained was dissolved in DMF (1 mL), filtered and purified by mass directed reverse phase LC/MS (1-99% ACN/H2O (5 mM HCl)) to yield 1-[4-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,6-dihydro-2H-pyridin-1-yl]propan-1-one (9 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ 9.28 (s, 2H), 8.58 (s, 1H), 8.18 (d, J=7.7 Hz, 2H), 7.80 (d, J=8.0 Hz, 2H), 7.63 (s, 2H), 6.66 (s, 1H), 4.30-4.13 (m, 4H), 3.70 (dt, J=16.2, 5.4 Hz, 2H), 2.71 (s, 1H), 2.59 (t, J=5.2 Hz, 4H), 2.41 (dt, J=21.8, 7.3 Hz, 2H), 1.03 (q, J=7.0 Hz, 3H). LC/MS m/z 420.5 [M+H]+.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customThe crude material obtained
  3. filtrationfiltered
  4. custompurified by mass

Sources & evidence

ORD record
ord-a77989c72ca143de9c74eed22e5c75c0
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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